8 Things Introverts Can Do to Get a Startup Job

The list of famous introverts is long and distinguished: Einstein, Mother Theresa, Warren Buffett, and Marilyn Manson to name a few. But would any of them stand a chance at getting a job at a startup?

Working at small companies has always appealed to certain people, regardless of personality type. It just didn’t used to mean you wore insanely orange sneakers to work, batted a ping-pong ball around, and broadcasted your entire life for the world to see.

And it’s hard to argue that a climate like this doesn’t favor extroverts. So how can introverts get noticed?

In a way, our company, Wakefield Media, might even be complicit in bolstering the ‘extrovert premium.’ We produce the largest startup careers event in the country, called Uncubed. Because job fairs have always been instruments of torture, we re-imagined the format. We injected energy anywhere we could: startups bring bouncy castles and puppies, and we’ve had Nancy Huang DJ, you can also pitch an idea on stage and win a round trip flight. There’s craft beer on offer, too.

It’s boisterous. And it probably is easier for extroverts to make connections in an environment like this.

So while prepping for our New York event, one where a couple thousand people will try to connect with startups, I thought it was worth a look at how those who don’t rely on an outsized personality can effectively get through to startups.

Make the Simplest Connection

If you’re interested in a company, follow them on Twitter and Like them on Facebook. You’ll get additional insight into who they are and how they operate. We’ve seen recruiters check and then discount applicants who say they love the brand but don’t follow it. It takes five minutes, and you may as well take this risk right off the table.

If there’s a newsletter, sign up. To stay organized, create a new folder in your inbox for your job search, and create a filter to send all of these emails there.

Sleuth

There’s no better compliment you can give a company than to know their history, and there’s no faster route to getting dinged than going up to a company and asking what it is they do (which happens with shocking frequency at our events).

Startups put everything out there on the web. You can easily find every piece of press every written about them. You can follow their history through their blog. You can read product updates.

Let’s use a real example: suppose I want to get a job at Contently, the marketplace that connects brands and writers. Here is my approach to learning about them:

My first stop would be their ‘About’ page. I might also check out their profile on Crunchbase for some basic details.

On their ‘About’ page, I notice they have a Manifesto. I give this a quick read, noting that the headline is “Original storytelling wins.” I immediately realize that this is the most important thing to them. If I get to speak with them, I’m going to bring this up early in the conversation and often.

Next stop is the Press page -- this is great fodder for things to talk about if I meet them or even touch upon in a cover letter. The first two posts are juicy. They just raised money -- $9 million. The article predictably says what they’ll spend it on, and this is critical information because this is where they’re going to apply resources. Among other things, they intend to create a ‘Nielsen-esque data and reporting’ tool. It also lists a number of their clients including TD Ameritrade and Ghirardelli Chocolate Company. Maybe later I’ll look and see if I can find any mentions on the web of those exact campaigns…

As a total bonus, I see that the press contact is actually a founder, Shane Snow, and his email address is listed right there. Failing everything else, I can now send a direct line to him.

I’ll also do a quick web and social search for what their community thinks, and what the company is posting about right now. As of this post, there are tons of tweets on the @Contently account about the social vs. search debate -- if I don’t know anything about this, I should read up.

Be a User

Even if you’re pursuing dozens of companies, you should try all of their products where feasible (you may not be able to use a B2B product, for example). The process itself will teach you a lot about products and that’s actually reason enough to do it, but it’ll also make you immediately relevant to the companies. And if you’re advancing in the process and serious about the company, then you should go to great lengths to do this.

Here, let’s use cash transaction network PayNearMe as an example. I go to the site and select ‘Make a Payment.’ This is going to send me on a field trip because I have to go to a retail location to complete the payment. But after doing so, I’m going to have the end-to-end user experience to talk about. PayNearMe seems like a service I might not naturally use, and if that’s true for others that might be applying, I’ve got a huge advantage by having tried it.

I’ll be sure to respectfully note a few things that I think could be improved, and a few things that I think are being done well. I can use these in cover letters or an in email approach -- done right it’ll get their attention.

Write by Hand

The New York Times ran something the other day called the “Found Art of Thank-You Notes.” It’s true, we get too much digital input. Emails are nice and efficient, but totally devalued by the volume around them. Send a hand-written note after a phone call or an email exchange and cut through the noise.

Everyone appreciates the thought, and it’s particularly valued at startups with a refined design sense or a very particular aesthetic; it feels measured.

Find a Very Specific Niche

Hone in on one very specific thing you can do for that company. Going back to Contently, maybe I think I can help with growth, broadly. But it’s worth focusing on one piece of that -- say, user acquisition. So I start getting smart on user acquisition for networks like this. I can pretty easily glean that they are probably very interested in attracting more high quality writers. I’d develop a basic strategy for how to do this, thinking through questions like these:

How can I activate writers on the network to recruit more writers?

Does paid acquisition make sense here (you’d have to make a guess of what the expected return is)?

What partnerships will make the most sense?

The conversation can turn to another one, but if I start with a very specific focus, it usually is an attention getter.

Be the Most Organized

Literally, as I was typing this, I got an email from an intern candidate we are interviewing. I haven’t opened it, but I don’t have to. I already feel urgency in wanting to reply. The subject reads, “Second Follow Up Technical Intern Opportunity”. It’s true, I haven’t followed up since her last inquiry. I’m guessing she has a calendar and an alarm went off for another follow up. It also helps that she knows how to write an email subject.

There are three other candidates that we’re considering. In my head, I just put her at the top of the list.

Solve Something

This is not as intimidating as it sounds. Recommend something about their product or the usage of it. For PayNearMe (and this is contrived because I actually haven’t used the product), maybe there’s something you would have liked to see on the PaySlip when you started the transaction, like a tip on new locations that have just opened up nearby. Or for Contently, when I signed up for their newsletter, I got an email asking for me to confirm my opt-in. It might be interesting to suggest removing this, to reduce the friction. They may tell you that it’s there to send the message that they care about their community, and they take the security of their members seriously. But it’s probably a worthwhile debate.

This is a great wedge tactic for getting the attention of a recruiter or a founder.

Find Like-Minded Companies

Not all startups are ping-pong-addled funhouses. Lots are more serious, and they have other ways of making it an attractive culture. Even calling out the absence of those things in your note to them can be a successful tactic.

So, while many of these seem obvious, we see very, very few people that do them all well -- introverted personalities or not. If you do, you’ll stand out, even against the loudest voice in the room.

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One of my favorite tips you listed was to write notes by hand. That truly has become a dying art! Also, if forces you send the note by mail which is interesting because people today don't receive "notes" in the mail when the majority of communication is done online.

Great article. It just goes to show you that little things, done right, matter.